- update firmware by dropping a file on the flash - instead of the button and updater software

Not possible with the current hardware, but maybe the next-gen one. The problem here is the bootloader, which cannot be replaced without risk of bricking the device, has very limited functionality.

However, I plan on removing the need to push the button, and roll the update functionality into ISO Manager while keeping it as a portable executable, no installation required. Prettymuch just a way for ISO Manager to tell the isostick to jump into its bootloader to accept an update, but the update would still go out over USB serial. See here.